Love and Heartbreak
by ThePagesFlyBy
Summary: One-Shot. Jess sees Rory's engagement announcement in the paper and heads to Stars Hallow to do...well he's not sure. This is what he comes up with.


**Love and Heartbreak**

**Disclaimer: I don't own a thing. Just the hope that one day they will do something like an epilogue to the show and Rory and Jess will be together.**

He saw her name in the paper early on a Friday in June. A simple announcement with the names _"Lorelai 'Rory' Gilmore and Logan Huntzburger" _and a congratulations to the couple. A couple with strong last names; the perfect power couple. He was sure that Emily was happy about this; he, on the other hand, was furious. He knew she had just graduated Yale and that he was planning on moving. Every so often he would talk to Luke who always filled him in even when he didn't ask.

Jess knew he should leave well enough alone. He knew he should throw out the paper and go on with his day, but for some reason he just couldn't. In an impulsive move, he called in to his office, requesting a few days off. Once that was confirmed, he packed a bag, and got in his car.

On his way out of the city he called Luke. "Luke's" came the gruff answer from the other end. "Hey Uncle Luke" he said, knowing his uncle hated the term. "Jess," was the annoyed answer from the other end. "I'm heading into town for a few days," Jess informed his uncle. "Think I can crash with you?" There was silence for a beat until Luke gave a surprised yes. "Good," his nephew replied, "I'll be there by closing I think…and…thanks Luke." A simple, "You're welcome, kid" was his only answer.

He didn't know what he was going to do when he got there. All he knew was that he had to figure something out. He had this overwhelming need to shake some sense into Rory. Maybe he would talk to Lorelai and see what she was thinking. She couldn't be happy that Rory was marrying Logan. Then adding the fact that she was going to move all the way across the country with him… There was no way she could be happy about the separation of the Gilmore Girls.

True to his word, Jess reached Stars Hollow before the diner closed that day. The silence that encased the place the moment he walked in was deafening. The last minute diners watching as if he was a ticking bomb, just waiting to ignite. Curiously glancing around, Jess saw just what it was that had the diner so quiet.

Lorelai sat at the counter staring at him. It was common knowledge that the assumption of the town was that when Jess was there, trouble was bound to come. He was after all the bad boy that had captured the heart of their fair princess.

The two stared at each other for a moment; then Lorelai nodded as if they were communicating silently. Jess nodded back and headed up the stairs to the apartment above. Ten minutes later Jess heard the tell tale sounds that Luke was closing for the night, then the heavy footsteps on the stairs. The door opened and Luke walked in, then he sat quietly at the table. For a few minutes they sat in silence; each waiting for the other to speak.

"What is it that you think you can do, Jess?" The words seemed to echo around the apartment. Jess just shrugged. He really didn't know what his plan was with coming down to Stars Hallow. "I don't know, Luke" he finally admitted. "I just saw that damn announcement in the paper and couldn't think straight. I thought things were better after she and I had talked. She went back to school and started talking to Lorelai again. She's not supposed to be with a guy like him!"

There was silence as both men thought about what Jess had just said. "Someone like you?" Luke finally asked quietly. Jess sighed. "I don't know, Luke. I know that she deserves better then someone like Logan. Maybe not me, but not someone like him." They sat in silence for a little longer before Luke said, "Sounds like you have some thinking to do, Jess. I'm gonna go home. Feel free to make yourself some food downstairs, there isn't anything up here." Jess nodded his thanks.

The next morning Jess headed over to the Dragonfly to talk to Lorelai. She was working at the front desk when he walked in. "Hey" he said quietly, not knowing for sure what her reaction was to his being in town. She stared at him as he stood in front of her. "What are you doing here, Jess?" she said after a minute of just staring at him. "Can we go somewhere to talk?" He asked, wanting to not have an audience. She nodded and led him into her office.

"Again, what are you doing here, Jess?" She repeated. He sighed and ran his fingers through his hair. "I don't know," he admitted. "I saw the paper yesterday and just had to come." She looked at him. "Jess, I don't know what you think you can do. I'm not thrilled with the situation either, but she won't really listen to me. She said yes all by herself. And you know what? She's a big girl; she can make her own choices." Jess laughed nervously. "You can't believe that," he said. "You can't want her to marry that jerk." She looked out the window with a far away expression on her face "No," she whispered. "I really don't. But she said yes and despite what I want, she seems to really love him and want to marry him. If California makes her happy then all we can do is be happy for her." Jess was shocked. "California!" he exclaimed. "What's in California?"

"You don't know?" she asked. "Logan got a job there and she wants to have an avocado tree." He let out a laugh; only Rory. "Is she coming to town soon?" he asked. Lorelai nodded. "She should be here by lunch today actually." He nodded "Lunch at the diner, I assume." She smiled. "Of course" He nodded again. "Ok. Well I'll let you get back to work. I'll see you at the diner later." He got up to leave, but just as he reached the door she called his name. He turned to look at her. "I hope you can get through to her," she said. He shrugged. "Me too."

Jess spent the next few hours working alongside Luke while fielding questions from the townsfolk about why he was there. His only response each and every time was that he needed a break from the city.

Working in the diner brought back memories of his teenage years. That and looking at the door every time it opened and the bell rang. Finally, they walked in. Jess just stared, he couldn't believe how much Rory had changed since the last time he had seen her. Then she looked up and locked her gaze on him. As always, he was stunned at how blue her eyes were. He found that he couldn't look away, he was caught and he didn't mind one bit. She blinked and the connection was broken.

Stepping up to the counter, Rory had her eyes trained on the counter as if it were fascinating. "Huh," was all he said before moving to take the order of a couple at a table across the diner.

He continued to work around where Rory and Lorelai were sitting all the while feeling her eyes on him whenever he moved.

An hour later he watched as Rory got up from the counter, hugged her mom, and walked out the door with a jingle. Watching her walk away, Jess saw her step falter and glance back at him.

Jess put what he was holding down and told Luke he was going out. "Jess…" Luke warned. Jess just waved him off and walked out the door. He knew it was possible that she hadn't gone where he was headed, but decided to go anyway.

It was no surprise to him when he saw her sitting there, her feet dangling off the edge of the bridge and twirling a flower in her hand. She didn't look up when he approached or when he sat down next to her. Jess decided to just sit next to her quietly until she decided to say something.

After ten minutes or so she spoke. "Did my mom ask you to come and try to talk some sense into me?" Jess laughed. "No," he answered. "No one asked me to do anything. I saw the announcement in the paper and decided to come down. I needed the break from work anyway." She looked back to the flower in her hand.

"It's perfect you know." He shook his head, not understanding what she meant. "Or, at least it seemed that way. Gilmore and Huntzburger; the ultimate power couple. My grandparents adore him, I love him. It all seemed to be perfect, like this flower." She held the flower up so Jess could see it. "See how perfect it is? But we know that in an hour, it's going to be all wilted." She fell silent again. "Do you think your relationship with Logan is wilted then?" he asked her.

"I don't know!" she cried. "That's the problem. He left for California today to go finalize some stuff with the business. I don't know what I think anymore. He's easy, Jess. I know what is going to happen with him. I know how he works and what he does. He's just…easy." She sighed, sadly trailing off. He was surprised. Honestly, he was pissed that Logan had just up and left two days after having Rory say yes to his proposal. If it were him, Jess swore, he would have never left her side.

The string of curses that Jess was thinking was definitely impressive. He took a breath before saying, "Sometimes Rory, easy isn't the best way to go. Sometimes, having a little difficulty in life is a good thing." She kept her eyes on her lap, but Jess closed his eyes hoping that she would catch his point.

Finally she looked up at him. "What is it you want me to say, Jess? My whole point in coming home was to think, and now adding you to the mix… I just don't know what to do anymore!" With that she got up and stormed off the bridge.

Watching her walk away, Jess let the impressive string of curses out. Laying back on the bridge, he stared up at the clear blue sky wondering if he had done the right thing.

Nearly two hours later, Jess still hadn't come up with an answer. Deciding that he needed to get his mind off the situation, he got up and headed back to Luke's.

Entering the diner, he didn't even bother to speak to Luke. He just grabbed a pad and pen and began taking orders or refilling coffee cups. Before long, Lorelai came in for dinner; no Rory in sight. She sat down at the counter in front of where Jess was leaning against it-reading a book-and stared at him.

"What?" he snapped, finally fed up with the staring. "What exactly was it that you said to my daughter that made her come home in tears and go straight to bed?" She asked. Jess didn't answer, his eyes stayed glued to his book, even though they both knew there was no actual reading going on. "She's in her room crying her eyes out, Jess," Lorelai said softly. Jess cursed.

"What is it you want me to tell you Lorelai? Obviously she has some stuff to think about. You know Rory; once she's got the crying out of her system she'll make her pro/con lists and make a choice. Nothing anyone says is going to change that." They stared at each other some more.

"He would never have said that," she finally said. Jess shook his head angrily. "I don't care what he would say!" She smiled sadly. "I just mean that you know her, Jess; much better than Logan knows her. Maybe you're the one that she needs to be with." With that last parting line, she left the diner.

That night…or rather the very early morning. Jess woke to the sound of rocks hitting the window of the apartment. Glancing at the clock, Jess wondered what the hell was going on at 3:27 in the morning. Heading to the window, he cracked it open to see a figure in the street.

"Rory?" he called down softly. He saw her face tilt up towards him and cringed at the tear tracks that were illuminated by the street light.

He closed the window and threw on his jeans before heading downstairs and out the front door. She was standing there, waiting for him when he came out.  
>"What the hell is going on, Ror?" he asked hastily. "Are you ok?" A fresh round of tears was his only answer. Pulling her into his arms, he held her as the tears continued to flow. "Oh Rory, don't cry," he said, not quite knowing what to do aside from simply hold her.<p>

Finally, the tears subsided. "I called him," she admitted quietly. "It's midnight and there are voices behind him. Giggling female voices. Voices calling him back to bed, Jess!" Once again Jess let out a string of expletives, something he realized he was doing a lot today.

"Does it really surprise you?" he asked. "Hasn't it happened before?" She remained quiet despite the tears running down her cheeks. "Yeah," she finally admitted quietly. "But we just got engaged. I thought that it would stop by now." He shook his head, not knowing what to tell her.

"I ended it." she said into his chest. He took a step back, surprised. "What?" he asked sharply, holding her by the arms. "I ended it," she repeated. "I'm done. I've had enough. You were right all along. I don't belong with him. I don't love him like I should. I never should have said yes when he proposed, but I just didn't know what to do with everyone starting at me that night. I was so confused because with everything…" She cut herself off before muttering, "Geez. I'm rambling again."

He laughed. "The rambling I'm used to. I just hope that it wasn't something I said…" He trailed off. She shook her head and took a step away from him. "Yes," she said. "It was something you said, but in a good way. You made me think. You made me realize that it wasn't right; that I needed to get out. That relationship is toxic and I can't have Logan or the whole situation in my life."

He watched her pace, staying quiet because he didn't know what to say. They were both quiet for a long time before Jess broke the silence. "What did your mom say?" he asked. She flinched. "I didn't tell her," she admitted. "I came straight here for some reason. I don't know why. Why did I come here, Jess?"

"I don't know, Rory," Jess said slowly. "I think," she began, "I think that something between us changed today on the bridge." Jess swallowed nervously. "You came to my rescue," she continued, "you made me see. It wasn't the nicest way to make me see and we both know that I really didn't want to see it at all, but something happened." She turned to look at him.

He kept his head down, not meeting her eye. "You felt it too!" she accused. A beat later, he lifted his head and nodded. "Yeah," was all he said.

It seemed that the confirmation was all Rory needed because the second the word was out of his mouth she threw herself at him and captured his lips in a kiss. His arms automatically wrapping around her.

After a minute, he came to his senses. Pulling away, he both heard and felt her groan. "What are you doing?" She asked breathlessly. "Rory, we can't do this," he said, just as out of breath as she was.

The look of shock and hurt on her face made him want to take her in his arms again, but he knew that this couldn't happen. "I'm not saying that it can't happen at all," he said quickly, "But now is not the time. You just broke up with Logan. You need to sleep and make sure this is what you really want to do and is not just the product of a long, emotional night."

She stood still for a moment and Jess could tell that she was making a pro/con list in her head. She let out a deep breath. "Ok," she sighed. "You're right. I need to sleep, talk to my mother, call Logan, and tell my grandparents. I need to go get my stuff from the apartment soon and get it all back here. My grandmother is going to be so mad." He knew to keep quiet during moments like this.

"Will it happen at all?" She asked suddenly. He smiled and pulled her into his arms again. "Yes," he said into her hair. "Yes it will. I promise you that, but not now. When you have everything back on track and you're back in Stars Hallow. I'll come to you or you'll come to me. We'll make it work, Rory. This time, we'll make it work. I swear that to you."

And so in the middle of Main Street during the middle of the night, Jess made his promise to Rory. A promise they both vowed would come true.

**A/N: Thanks to xXSingSweetNightingaleXx for helping out and making sure it all makes sense. As always, let me know what you think.**


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